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Method for producing mixture of fluoroalkyl iodides

a technology of fluoroalkyl iodide and mixture, which is applied in the field of method for producing mixture of fluoroalkyl iodide, can solve the problems of low production efficiency and low selectivity of desired fluoroalkyl iodide, and achieve the effect of increasing the selectivity of a desired fluoroalkyl iodide and reducing production efficiency

Active Publication Date: 2015-12-15
DAIKIN IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to a method for producing desired fluoroalkyl iodides using a metal catalyst. This method inhibits the production of by-products, leading to higher efficiency and purity of the desired product. The method also utilizes multiple reactors to allow for separate, fast and slow reactions, resulting in higher selectivity for desired fluoroalkyl iodides. Overall, this method improves efficiency and purity of the production process and allows for adjustable reaction times.

Problems solved by technology

For example, when the desired fluoroalkyl iodide is 1-iodoperfluorohexane (C6F13I), many other fluoroalkyl iodides that have more carbon atoms than 1-iodoperfluorohexane (C6F13I) are also produced, which results in low selectivity of the desired fluoroalkyl iodide.
While such a method is also excellent, the method produces by-products represented by Rf—(CF2CF2)n—H (wherein Rf is any one of fluoroalkyl groups having 1 to 10 carbon atoms, and n is an integer indicating a degree of polymerization) due to the use of a peroxide as a catalyst for promoting the reaction, and the method requires a step of removing the by-products from the reaction system, which results in low production efficiency.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0080]A 200 ml-capacity stainless steel pressure reactor equipped with a stirrer was provided as a first reactor. The reactor was charged with 200 g of 1-iodoperfluoroethane (C2F5I) as a telogen and charged with 10 g of copper powder as a metal catalyst, followed by heating to 100° C. While the temperature in the reactor was maintained at 100° C., tetrafluoroethylene was supplied as a taxogen while stirring the reaction mixture to pressurize the reactor until the pressure in the reactor became 1.2 MPa (gauge pressure).

[0081]Then, while the above temperature and pressure conditions were maintained, and while 1-iodoperfluoroethane (C2F5I) was supplied at a flow rate of 133 g / hr and tetrafluoroethylene was supplied at a flow rate of 5.5 g / hr, a reaction, mixture was discharged from the reactor at a rate of 138.5 g / hr. A telomerization reaction was thereby performed. The obtained reaction mixture was cooled to give 1,255 g of a first reaction mixture.

[0082]This reaction mixture was dist...

example 2

[0086]A 200 ml-capacity stainless steel pressure reactor equipped with a stirrer was provided as a first reactor. The reactor was charged with 200 g of 1-iodoperfluoroethane (C2F5I) as a telogen and charged with 10 g of copper powder as a metal catalyst, followed by heating to 100° C. While the temperature in the reactor was maintained at 100° C., tetrafluoroethylene was supplied as a taxogen while stirring the reaction mixture to pressurize the reactor until the pressure in the reactor became 1.2 MPa (gauge pressure).

[0087]Then, while the above temperature and pressure conditions were maintained and while 1-iodoperfluoroethane (C2F5I) was supplied at a flow rate of 200 g / hr and tetrafluoroethylene was supplied at a flow rate of 5.0 g / hr, a reaction mixture was discharged from the reactor at a rate of 205.0 g / hr. A telomerization reaction was thereby performed. The obtained reaction mixture was cooled to give 2,254 g of a first reaction mixture.

[0088]This reaction mixture was distil...

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Abstract

The present invention provides a novel method for producing a mixture of fluoroalkyl iodides with high production efficiency, the method enabling the production of a desired fluoroalkyl iodide with high selectivity. Specifically, the present invention provides a method for producing a mixture of fluoroalkyl iodides represented by formula (I):Rf(CF2CF2)nI  (I)(wherein Rf represents a fluoroalkyl group having 1 to 10 carbon atoms, and n is an integer indicating a degree of polymerization), the degree of polymerization n being m or more (m is an integer of 2 or more) by telomerization in metal catalyst-containing reactors, the method including:(1) step 1 of reacting a fluoroalkyl iodide represented by formula (III):RfI  (IX)(wherein Rf is a fluoroalkyl group having 1 to 10 carbon atoms) with tetrafluoroethylene in the presence of a metal catalyst in a first reactor to obtain a first reaction mixture containing a mixture of fluoroalkyl iodides represented by formula (I) wherein the degree of polymerization n is 1 or more;(2) step 2 of separating the first reaction mixture withdrawn from the first reactor intoa first fraction containing a fluoroalkyl iodide or a mixture of fluoroalkyl iodides represented by formula (I) wherein the degree of polymerization n is (m−2) or less, a fluoroalkyl iodide, represented by formula (II), and tetrafluoroethylene,a second fraction containing a fluoroalkyl iodide represented by formula (I) wherein the degree of polymerization n is (m−1), anda third fraction containing a mixture of fluoroalkyl iodides represented by formula (I) wherein the degree of polymerization n is m of more; and(3) step 3 of transferring the second fraction, into a second reactor in which a metal catalyst is present and reacting the second fraction with tetrafluoroethylene in the second reactor to obtain a second reaction mixture containing a mixture of fluoroalkyl iodides represented by formula (I) wherein the degree of polymerization n is m or more.

Description

[0001]This application is a 371 of PCT / JP2013 / 056721, filed on Mar. 12, 2013.TECHNICAL FIELD[0002]The present invention relates, to a method for producing a mixture of fluoroalkyl iodides.BACKGROUND ART[0003]Methods for producing a fluoroalkyl iodide by telomerization are known.[0004]Such telomerization is conducted by consecutive reactions between 1-iodoperfluoroethane (C2F5I) as a telogen and tetrafluoroethylene as a taxogen in a reactor.[0005]For example, Patent Literature (PTL) 1 discloses a process for producing a fluoroalkyl iodide represented by Rf—(CF2CF2)n—I (wherein Rf is a fluoroalkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 4) by telomerizing a compound represented by the formula Rf—I (wherein Rf is a fluoroalkyl group having 1 to 6 carbon atoms) as a telogen and tetrafluoroethylene as a taxogen in a reactor in which a catalyst is present.[0006]While such a method is excellent, there is room, for improvement in terms of selectivity of the fluoroalkyl...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C17/278B01J23/72C07C17/383C08F14/26B01J23/02B01J23/06B01J23/22B01J23/32B01J23/34B01J23/42B01J23/46B01J23/50
CPCC07C17/278B01J23/72C07C17/383C08F14/26C07C19/16B01J23/02B01J23/06B01J23/22B01J23/32B01J23/34B01J23/42B01J23/462B01J23/50C07B61/00C07C11/08C07C11/12C07C11/18C07C11/20C07C11/22Y02P20/584
Inventor HIRASAKA, TAKEOMI
Owner DAIKIN IND LTD